Convergence of Catalytic Antibody and Terpene Cyclase Mechanisms: Polyene Cyclization Directed by Carbocation-π Interactions

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Abstract
A tandem cationic cyclization cascade similar to a terpenoid cyclase reaction is catalyzed by antibody HA5‐19A4. The 2.7‐Å resolution crystal structure of the Fab–hapten complex reveals convergence with the same catalytic strategy employed by a terpenoid cyclase: both serve as templates that enforce the productive conformation of a flexible polyene substrate, and both stabilize carbocation intermediates through cation–π interactions with multiple aromatic residues in their active sites.